Trifluoroacetic acid → 3-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959407노트

반응식

HRID 1959407 반응식
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:27]2[N:31](C(OC(C)(C)C)=O)[C:30]3[CH:39]=[CH:40][CH:41]=[CH:42][C:29]=3[N:28]=2)=[N:11][C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH:20]=2)=[CH:13][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[C:29]2[CH:42]=[CH:41][CH:40]=[CH:39][C:30]=2[N:31]=[C:27]1[C:10]1[C:9]([NH2:8])=[N:14][CH:13]=[C:12]([C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH:20]=2)[N:11]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66745113Tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate

생성물 1

HCID 667455743-(1H-benzo[d]imidazol-2-yl)-5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine수율 14.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl 2-(3-(bis(tert-butoxycarbonyl)amino)-6-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-yl)-1H-benzo[d]imidazole-1-carboxylate (100 mg, 0.1495 mmol) in DCM (1 mL) was treated with TFA (1 mL, 12.98 mmol) and allowed to stir at ambient temperature for 40 minutes. The reaction was concentrated in vacuo and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a pale brown solid (8.0 mg, 14% Yield). 1H NMR (400.0 MHz, DMSO) d 2.84 (2H, m), 3.53 (2H, m), 3.94 (2H, m), 6.76-6.90 (3H, m), 7.20-7.69 (6H, m), 7.70-9.39 (4H, m), 12.88 (1H, m) ppm; MS (ES+) 369.02

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  3. customThe fractions were collected
  4. customfreeze-dried

출처 및 근거

ORD 기록
ord-9acc32b305194e87b1a50b2148df2df4
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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